Hope of a Simple Man
by ShadowObsessor01
Summary: Dean is traveling alone after John's and Sam's massive fight over Stanford. On a routine hunt, he is gravely injured and ends up spending three weeks recuperating in Tallahassee, Florida. While there he meets a very interesting young woman with haunted green eyes.


Language warning because Dean is a potty mouth. Though it's not too terrible. This is a part of my Madness of Hope series, it will be a short off-shoot, with one more definitely planned addition with a possible third. I'm thinking out the logistics. Please let me know what you think!

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 **Hope of a Simple Man**

Squinting through the haze of smoke and spotlight glare, Dean Winchester wondered again how he ended up here. Okay, not here as in Tallahassee, he knew very well how he got there, but here as in on a corner stage in a diner bar preparing to quite possibly humiliate himself. A flash of gold in his peripheral brings his gaze to meet with laughing viridian eyes. Oh, right, he's up here because he can't say no to a pretty face. _Damn._ He can't even really be mad at her. Emma Swan is a breath of air Dean hadn't realized he needed until she turned down his advances but offered something better: a listening ear. Dean has seen too much evil to believe in an all-seeing God, but he can't really explain away meeting Emma, Dugan and Morita as a coincidence.

A gusty sigh echoes through the microphone as he absentmindedly plucked a guitar string. It had been a little while since he had held let alone played a six string acoustic, but it was much like riding a bicycle; you just never quite forget. And this song...this one he knew almost as well as his Baby.

"Uh, yeah...Hi. C-can y'all hear me out there?" A few assents were good enough for him. "Yeah, so I'm being blackmailed into this and I can't really promise Ronnie Van Zant levels of greatness, but, uh, heard this song a few years ago and well, it, um, it's got alotta meaning for me. So, uh...yeah here goes my reputation." That got a few chuckles from the more sympathetic crowd.

The beginning chords for Lynyrd Skynrd's Simple Man was a better calming agent then a cold beer. If he could justify keeping a guitar case in Baby and the hurdle of his big bad rap among the supernatural and hunter population going down the drain for it, he would have purchased the instrument ages ago.

 **Mama told me when I was young  
Come sit beside me, my only son  
And listen closely to what I say  
And if you do this  
It will help you some sunny day**

 **Take your time...don't live too fast  
Troubles will come and they will pass  
Go find a woman and you'll find love  
And don't forget son  
There is someone up above**

Dean opened his eyes, hazel green seeking out the young blonde waitress that is a refreshing sunshine enigma in his dark, shadowed world. Emma Swan is sarcastic and blunt, realistic and strong. She reminded Dean of him and his brother. Sammy would have loved her. His mother would have loved Emma too. That's not even taking into account how much her and Jo would get on ( _a house on fire doesn't even cover it!_ ) or how Ellen would mother Emma. Bobby would spoil her in his own gruff way, possibly give her one of the fixed up classics ( _Emma would look sweet and pretty behind the wheel of the '65 Mustang_ ) and turn down any payments on upkeep. Watching the honey blonde curls bounce as she sashayed between tables, dancing to the song, Dean could see what having a sister would have been like.

Emma as a Winchester would have been like coming Home.

 **And be a simple kind of man  
Be something you love and understand  
Be a simple kind of man  
Won't you do this for me son  
If you can?**

Four days ago, Dean had pulled the Impala into Tallahassee, thoughts only on the creature snacking on humans, trying to drown out the silence the absence of Sammy and Dad had brought. He was an adult and so was Sam but for so long it had only been the three of them against the world. Now Dean was alone and it was hard, so damn hard, to put another mile under the Impala's tires, another fugly six feet under and another victim's family at peace.

There wasn't enough beer or pie to drown out the loneliness overcoming him. Dean is one of those guys who does NOT chick-flic moments, but he was man enough to admit to himself that he needed company. Most of the time he could get through on one night stands, but then again, during those times he had Sam back at a motel or at school or in the local library studying. There would be someone to come back to in the morning so really, he wasn't alone. This...hunting alone...

He didn't like it.

Hated it though really he understood why Dad left and why Sam abandoned them. Dean is an adult, he doesn't need his dad to be at his back giving him pointers and holding his hand. Doesn't need to take care of Sammy anymore, because his little brother is grown now and can care for himself. His family doesn't need a drop-out screw up with too much attitude and an ever increasing drinking habit. Dean can't be honest with anyone but himself, because all he has is himself.

It's easier to ignore the days and nights when loneliness consumes him faster than the bottom of the bottle greets him so long as the blood of monsters puddles at his feet. When another family is saved because Dean put down the creatures of the dark gunning for flesh and blood and life, he can ignore the craving for companionship beating in his heart. In the light of day he refuses to acknowledge chick flick moments, but his dreams play out the words he can't say.

In dreams he can cry. In dreams Mary is there to hold him and listen and tell him that he is loved. That he isn't the same as the monsters he puts down.

Dean hates waking up.

 **Forget your lust for the rich man's gold  
All that you need is in your soul  
And you can do this if you try**  
 **All that I want for you my son  
Is to be satisfied**

The signs had all pointed to a werewolf pack hunting in Tallahassee, Florida. A job most solo hunters would turn down because of a lack of back-up. Dean is reckless and cocky and damn proud of the skills he's rightfully earned through soul-crushing work. He's been raised in the life. Hunting his entire life has made him strong, stronger than most Hunters. A pack is worrisome, but not impossible.

He's a damn fool. An idjit, as Bobby so rightfully shouted down the phone line afterward. He took out the pack but was laid up for three weeks healing. The _Fallen Brother Bar and Diner_ became his sanctuary, the place to drown the pain and loneliness with cheap whiskey and some of the best burgers he had ever tasted. It was also the place where he met one Emma Swan, an enigma bundled together with green eyes and blonde curls, more sass and fire than a house cat, in a package Dean could have crushed in a gentle hug. She was so tiny compared to Dean and practically microscopic compared to Sasquatch Sam. But her presence gave her height and she would have none of Dean's shit.

He kind of loved her for that alone.

Dean had gone in the third day after hunting the pack, sore and with more bruises than unblemished skin, with all the local papers he could find to search for the next Hunt. He might not have been able to take Baby and drive to any one he found, but the great thing about being a Hunter meant that sometimes, if one Hunter was down, he could research and give the information to others. As a general rule, Hunters trusted no one, not even other Hunters, but all believed in the cause so tips were accepted and cross-referenced for validity before being acted upon. Just because you had a personal chip with a fellow hunter for being a jackass on a different Hunt, did not mean that grievance prevented you from taking another job tipped off by the other. It was an unspoken rule that John Winchester had been hard-pressed to learn. Dean was much the same, however, he had an easier time putting differences aside to get the job down. Usually.

He had spent at most an hour looking through the various pages, circling potential leads and cross-referencing unknowns with his journal when she had come to his table. Obviously a waitress, the petite blonde standing in front of his table was absolutely adorable. Corn silk hair pulled up into a wavy massed ponytail with strands framing a heart-shaped face. Eyes a purer green than his own assessed him. _Oh, she's gonna be a fun challenge._

Dragging his bottom lip down with the pen he had been unconsciously tapping it with, Dean smiled in a way he knew from experience most women couldn't resist. She did. In fact, she rolled those emerald eyes before pointedly clicking her own pen and posing it over a blank pad.

"What can I get for you?" She didn't have a local accent and certainly not enough of one that he could place where she was from. Added to the hostility seeping from her pores, Dean almost vibrates from excitement. _Wohoo yeah! Definitely a challenge._

Digging out the menu from its burial under newspaper, Dean skimmed it to refresh his memory.

"Well, Darlin', I'll take one of your delicious sounding Bacon Deluxe Burger, a cold beer, and lets round that all out with a hot slice of this famous apple pie." Dean was throwing the full weight of his charm at the pretty waitress. From experience, he knows he can be very charming, but something told him this woman would be different. And he always trusted his instinct.

She was unmoved ( _Shocker_ ), simply writing down his order before turning those intriguing emerald eyes to him.

"Anything else? Fries? Onion rings? A nice healthy dose of humility?"

Dean couldn't help it: he laughed. Maybe not a full barreled laugh, and even what he was doing now pulled painfully on his slowly healing ribs, but the utter **snark**...

Sammy would have loved her.

"Rain-check on the humility, but I wouldn't mind getting' your number, Gorgeous." His words still heavy with the sudden humor that had taken him. As she turned away, rolling her eyes all the while, he couldn't help making one last request.

"And maybe some ice for this lovely burn?" Totally worth it to watch her freeze and regard him silently though he wouldn't guess at the emotion flitting over her face. Dean didn't know her well enough for that, but maybe...

When she returned nearly thirty minutes later with his food, the burger patty was a charcoal lump, the bacon dangerously undercooked, the beer was warm and some kind of fruity sweet and sour number that he gagged on, and the pie was ice cold. Not the best way to eat a pie but it hadn't been entirely ruined like the others so he happily munched on it while he watched her interact with the others patrons.

Suddenly, the next three weeks or so of recovery didn't seem quite so horrible. Because she had also brought one other item with her.

A large ziplock bag of ice.

 **And be a simple kind of man  
Be something you love and understand  
Be a simple kind of man  
Won't you do this for me son  
If you can?**

It took five days of asking and generally being a nuisance before she finally cracked. And most of those days he was extremely grateful for his cast iron stomach. That woman knew way to much about ruining food to the point of poisoning.

"It's a gift." Dean blinked in surprise, staring up at honestly amused green eyes.

"Well...Shit. I said that out loud, didn't I." Giving his fellow blonde a self-deprecating grin, Dean closed the German mythology tome he had been using for research. He barely had the notes and loose papers cleaned and stacked when she sat down. Dean stared at the precocious blonde in surprise. This was entirely out of the norm for her in their "relationship" and left the young hunter slightly dazed. It somewhat amazed him how easily he had fallen into a routine with the woman and now to have that routine changed, Dean wasn't entirely sure how to proceed.

So he stared at her and she at him and neither spoke against the awkward tension.

"Why?"

Until she did.

"Why what?" It was an honest question for him. Her asking him 'why' could have been a question for a great many things. Why was Dean so handsome? Why does he read such obscure texts? Why does he frequent this diner? Why does he have such a kick-ass car?

"Why do you keep asking for a number I have very clearly stated you will never get?"

Oh, that 'why' question.

 _Hm, how to answer..._

"I like a challenge."

She seemed to be buying...for all of three seconds.

"Mm...Nope try again."

"What?! That's the God honest truth! You're a challenge, one that will stave off my boredom while I'm stuck here."

"No, that's only the surface part of it. If you are ever going to have a chance at me, better be truthful."

"And if I don't feel like divulging more?"

"I get up from this table, go to the kitchen and see how hot you can take your jalapeno pie."

"You wouldn't!?"

"Try me."

Dean scanned her face, trepidation and irritation bubbling in his stomach. Why couldn't she take his words at face value like everyone else? Why **wasn't** she taking everything at face value? It's not like she knew him. She had been rejecting him for the last five days. The only verbal interaction between them was short moments of banter. So what gave her the right to assume she **"** **knew"** Dean? A soft snarl built behind his teeth, anger and hurt and fear battling for dominance as he stared down the aggravating blonde.

Cool, hard emerald eyes stared down his own hazel-green.

 _Dammit, she's got one bitchin' resolve face. Shit!_

The snarl died out into a weary sigh.

"Fine, alright," Dean scrubbed his face with his hand, trying unsuccessfully to wipe away the roiling emotions. "Just...just, don't defile the pie, please." He gives her his best puppy eyes, the ones that always worked on Sammy, _on Mom_ , and seems to have worked on his enigma of a waitress because her eyes lose the jaded harsh look and warm in a way he only remembers from a childhood not touched by darkness. She smiles and it's not like the smiles from the last five days, bitter and cold, never reaching the emerald gems she calls eyes. This smile is bright and hot and full of playful life. Dean feels like he's been sucker punched by a shape-shifter. Her smile was like how Sam's used to be, before he hit puberty and before the malevolent tension between him and Dad grew. When Sam was innocent and all he needed was Dean to love him and care for him and be both older brother and father in John's absence.

Then she laughed. Dean didn't think he had ever felt more pole-axed than in that moment. It was Sam's laugh, and Mom's laugh, and Dad's laugh before everything went to Hell in a hand-basket. It was a Family laugh: light and life and love; happiness and insider secrets; **acceptance.**

"You must really like pie, huh."

"It's God's greatest gift to man!"

"Besides yourself?"

 _Damn, the_ _ **sass...**_ Dean laughed, harder and longer than he could ever remember laughing before. Other patrons started to look, to notice him and his unguarded state, but for once, Dean didn't care. He was **happy** , in a way he had only felt a fraction of a handful of times in the past and certainly not since Sam left for college.

"You're alright, kid."

"Ain't a kid, Pretty Boy." But she's smiling still, her chin propped up on one dainty hand while her eyes tell him of the tentative hope growing. Dean offers her his good hand, the opposite shoulder heavily stitched and aching from his sudden bout of humor.

"Dean."

She takes his hand, her own tiny but somewhat rough, speaking more for the hard life he's guessed at in her actions.

"Emma." They shake hands, both exalting in the warmth of another soul kindred to their own before reluctantly letting go. Emma gives him another smile as she stands from her seat.

"Apple, right?"

Dean hates chick-flick moments, the tears and the feelings rubbing against his macho-masculine persona. But...Hot DAMN, if he doesn't feel like crying at the genuine acceptance in young Emma, so reminiscent of his brother before John's repeated broken promises shattered any innocence left.

"Y-yeah. Apple's the best type of pie, though I'd eat just about any flavor."

"I prefer blueberry or chocolate myself."

Emma leaves and comes back a few minutes later with a large slice of warmed apple pie topped with vanilla ice cream, a large coffee and a cup of hot chocolate with whipped cream sprinkled with cinnamon. They talk, about everything and nothing, until her break is over and she goes back to work.

Dean falls asleep that night easier than he has in weeks and wakes actually looking forward to the day.

 **And be a simple kind of man  
Be something you love and understand  
Be a simple kind of man  
Won't you do this for me son  
If you can?**

Dean heals both physically and, if he's honest with himself, emotionally, during his stay in Tallahassee. He keeps in contact semi-regularly with John, and hacks Stanford's security cameras and network daily. Bobby is called whenever he pinpoints a case, giving the gruff man the information to pass on to the nearest hunter. Normally, after the first week, Dean would be chomping at the bit to keep moving, to keep hunting, to Hell with waiting to heal properly. This time though, a pair of green eyes and a mouth of sass keeps him occupied from going hunt-crazy. Emma is a God-send, if he believed in that kind of crap. But, crap or not, Emma was a special case in Dean's world. After that first truce, any lustful thought of her went the way of the monsters Dean hunted. He couldn't picture her as another one-night stand, a slutty chick to bang and forget. No, Emma was way too classy for that. To Dean's own surprise, he began to see her as a sister, which is not a title or feeling he gave out all willy-nilly especially in his kind of work. Which he hadn't told her about. However, he did begin carving warding symbols all around the building by the middle of his second week.

The carvings were the result of his first nightmare involving Emma and whatever killed Mary. He woke up barely biting back an agonized scream, sweat pouring down his body and soaking into the cheap motel sheets. If Emma noticed he seemed to watch her a lot more closely or the fact that he hovered around the entrances and exits, she didn't speak up. Not that she had to what with the quickly perfected _what-the-hell-is-your-problem_ look she gave Dean. He was confronted about the carving three days after that by Tom, the absolute mountain of a bartender that would give his Sasquatch of a brother competition. Tom spoke like he had thunder rumbling in his chest, cast a shadow over Dean like a personal solar eclipse, and absolutely did **not** _ **question**_ Dean when he spoke of the supernatural. Tom just smiled, a secret dancing in cornflower blue eyes before issuing one of the scariest warnings Dean had received from a father figure.

"Break her heart and I'll only break you in half. The cook, John Morita? He'll dice you into tiny slivers and use those pieces to bait his fishing hooks."

Dean got the warning **exceedingly** clear. After that though, it wasn't uncommon for Dean to find Tim or John joining him while Emma worked. He already figured out that their names were alias, however, anything more than that was to hard to find with the resources Dean had at his disposal. He asked Bobby to look into the two but so far there was jack squat. At the same time, he didn't really mind not knowing. Both men were hilarious in their own way and fed off each other in a way Dean only dreamed of ever having.

Maybe one day...

 **Boy, don't you worry...you'll find yourself  
Follow you heart and nothing else  
And you can do this if you try  
All I want for you my son  
Is to be satisfied**

The night before Dean was set to leave, the staff of the _Fallen Soldier_ threw a small going-away party. It was nice. The food was good, as always, and the music a surprisingly tasteful mix of pre-World War II swing music and Dean's own personal favorites from mullet rock. Emma was a bubbly whirlwind, twirling and dancing her way through the party-goers. Dean even managed to snag a couple of dances with the young woman he personally considered a little sister. Tom and John had packed him a large cooler of food and his favorite beer, with their personal number added to "give them a call next time he was in town or if ya just need to rant about a case and can't find a decent conversationalist wherever you're at". Emma had given him a hand-woven leather bracelet with low-grade gemstones and protective charms intertwined in the strands. Her sheepish look had been absolutely adorable when she explained that John had helped her pick out the stones and charms while Tom had guided her through weaving the parts into a finished product. Dean never took it off.

Later when midnight rolled around and Dean's cheeks had finally lost the heated blush of embarrassment from all the praise of his singing, he found Emma on the roof, sitting and watching the stars spin. All was quiet between them after he sat down, both just soaking in the presence of the other, neither needing to say anything to break the silence.

"Do you ever sit to just watch the stars and wonder...is there something...better waiting for me? Or is _this_ all I'll ever have? The emptiness and guilt and just...is that all there is?"

Dean said nothing for a long time. What could he say to questions like that? Questions he asked every damn day since his mom...

"Yeah. I wonder...if I did this differently, would I have been able to save this person? If I said this, would someone else have stayed instead of left? Ifs and wonders aren't any way to live, but we still live asking them, pondering the things we have no right to do so. The answer may seem so Hallmark, but it is in its own way true: we are only human. I wonder every day if things would be different had my mom lived, if my dad had died instead, if Sammy didn't aggravate dad so often would he still be here? Yeah, I wonder and then I let it go, because dwelling on things that will never be makes reactions slow and that's just begging for death. You can't live for the past, Emmy, and maybe you can't live for the future yet, but you can live for the present. Tom and John, they're good people and they love you dearly. You shouldn't make them worry by being all depressed."

"This time last year, I was in jail and pregnant."

Okay, he did not expect _that_ to be her reply to his verbal spew. It also raised a shit-ton of questions. Dean kept his silence though, watching her out of the corner of his eye, seeing tears pool and splash silently down her cheeks. She didn't need him to talk, just listen.

"I thought I loved him, thought he loved me too. But something spooked him, from his time before me, and I wanted to help and I thought I was...but then the officer came and he wasn't there. He sold me out to save his own skin. You can't imagine how dead I felt inside, D, looking at that stick while sitting on a hard cot behind bars. Oh, but he thought he could make things all better by leaving me our stupid CAR!" Emma is up and pacing before him, her voice rising and falling with the storm of emotions. Dean sits and tracks her, lets her release the tension from her frame and from her soul. Because he knows that sometimes, a good rant is all one needs to move on and keep functioning. Several trees throughout the US of A harbor Dean's secrets (though all were carefully vetted before he started ranting. There's no telling what supernatural fugly might be contained in a tree!).

"I would have given everything to keep my baby! Everything! But I was just a kid myself and in jail and maybe I could have sent him to Aunt Charlie but she didn't need to clean up my crap, doesn't deserve that. Oh.. _God,_ D! I..I couldn't even _look_ at my baby before they took him. I don't know if he's got my nose, or his eyes, or just how perfect his hands and feet are. All that pain...why couldn't I look!?"

Dean gathers his sobbing sister carefully to his chest, rocking her back down from the emotional roller-coaster she went through.

"You didn't look, Emmy, because you would have kept him otherwise. That doesn't make you a bad mother. It just makes you...human. That's not something to be ashamed of, Lil' Sister."

She stills in his arms and for a moment, Dean scrambles to think of what he had said to offend her.

"Little...sister?"

Oh! Oh... _shit..._

"W-well, you see...it just...and...uh... **crap!** "

Dean stumbled over his words, cursing himself for sounding like some pre-teen hormone bomb trying to talk to his crush instead of the twenty-three year old smooth operator he's become through experience. Then Emma giggled and Dean stopped sputtering to stare in silence at the blonde enigma in his arms. Despite only knowing Emma for three weeks, he had never actually heard her giggle like..well, like a girl. Emma was hard laughter and barking huffs, not twittering bird song. And yet...it sounded nice, coming from this young girl his beloved brother's age. A tentative smile pulled at the edges of Dean's mouth, answered by one just as timid yet infinitely more brilliant.

"I...I like that. Being a little sister, I mean."

"Y-yeah?" No, Dean Winchester, Bad-ass Hunter, did NOT squeak.

"Mhm. I..I don't have a lot of luck with families so...please...be careful out there...Brother."

If Dean cried, just a little, at the word brother spoken to him by this amazing, fantastic young woman; well, that was no-one's business but his, the stars, and this precious woman who wanted to be his sister.

Driving away the next morning was one of the hardest things Dean had to do. However, the pain was helped along by the presence of two new phone numbers and a picture.

A blonde young man with an arm slung around the shoulders of a petite blonde girl, a short but wiry Asian American man standing to the left while a bear of a man with auburn hair stood behind the two blondes. All were smiling. All had laughter dancing in haunted eyes. But the best part of the photo was the feeling of one thing they all craved:

Family.

 **And be a simple kind of man  
Be something you love and understand  
Be a simple kind of man  
Won't you do this for me son  
If you can?**


End file.
